Tris-trimethylsiloxy amines

ABSTRACT

Amines of the formula (Me3SiO)3Si(CH2)3NHMe and (Me3SiO)3Si(CH2)3NMe2 are useful as bactericides and fungicides.

United States Patent 1 Michael et al.

[ 1 March 6,1973

TRIS-TRIMETHYLSILOXY AMINES Inventors: Keith W. Michael; Yolanda A.

Peters, both of Midland, Mich.

Assignee: Dow Corning Corporation, Midland,

Mich.

Filed: Sept. 29, 1971 Appl. No.: 184,917

U.S. Cl. .....260/448.2 N, 260/448.2 E, 260/999,

260/DIG. 9 Int. Cl. ..C07f 7/10 Field of Search ..260/448.2 N

Maki et al., Yukagaku, l9, (1 1) November 1970.

Primary Examiner-Daniel E. Wyman Assistant Examiner-P. F. Shaver Attorney-Robert F. Fleming, Jr. et al.

[5 7] ABSTRACT Amines of the formula (Me SiO) Si(CH NHMe and (Me SiO) Si(CI-l NMe are useful as bactericides and fungicides.

3 Claims, No Drawings The composition (Me SiO) Si(CI-l NMe is disclosed by Maki et al, Yukagaku 19 (11) November 1970; Chem. Abstracts 74(8)32907 Feb. 22, 1971. Applicants made the compounds of this invention prior to November 1970.

The compositions of this invention are useful as surfactants and as bactericides and fungicides. The latter utility is claimed in the copending application of Eugene A. Abbott and Alan J. Isquith entitled Method of Inhibiting the Growth of Bacteria and Fungi Ser. No. 1 84,918, filed concurrently herewith.

This invention relates to amines of the formula (Me SiO) Si(Cl-l NMe,,I-l in which n is an integer from 1 to 2.

In the specification and claims Me is the methyl radical.

The amines are made by reacting Cl(Cl-l,) S i(OSiMe with methyl or dimethylamine. The silicone starting material is made by cohydrolyzing Me' SiCl and Cl(CH i(OMe) The following examples show the preparation of the compositions of this invention.

EXAMPLE 1 0.4 mol of dimethylamine, 0.2 mole of (Me SiO) Si(CH Cl and ml. of hexane were placed in an autoclave and heated at 200C for 4 hours then allowed to stand overnight. The dimethylamine hydrochloride was removed by filtration and the filtrate was distilled to give (Me SiO) Si(Cl-l NMe b.p. 78C at 5 mm.

EXAMPLE 2 A mixture of 0.107 mole of (Me SiO) Si(CH Cl, 0.62 mole of methylamine and 50 ml. of hexane were heated in an autoclave at 200C for 4 hours then cooled overnight. The methylamine hydrochloride was removed by filtration and the product distilled to give (Me SiO Si(CH NHMe boiling at 68C at 5mm.

That which is claimed is:

1. An amine of the formula (Me SiO) Si(CH,) N- Me,,l-l, in which n is an integer from 1 to 2.

2. The compound of claim 1 in which n is one.

3. The compound of claim 1 in which n is two.

U.S. PATENT OFFICE UNITED STATES PATENT OFFICE CERTIFICATE OF COERECTIOIE Patent No, 5,719,697 D March 6 19? Keith W. Michael and Yolanda A. Peters It is certified that errors appear in the above-identified patent and that said Letters Patent are hereby corrected as show below:

Column 1, line 22, the formula "01(CH2)3i(O1 le)3 )S i OM I should read Signed and sealed this 27th day of November 1973.

(SEAL) Attest:

EDWARD VLPLETCHERJR. RENE D. TEGTMEYER Attesting Officer Acting Commissioner of Patents 

1. An amine of the formula (Me3SiO)3Si(CH2)3NMenH2 n in which n is an integer from 1 to
 2. 2. The compound of claim 1 in which n is one. 